(Z)-5-undecylidenethiazolidine-2,4-dione | 1227475-10-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (Z)-5-undecylidenethiazolidine-2,4-dione
• 英文别名: (5Z)-5-undecylidene-1,3-thiazolidine-2,4-dione
• CAS: 1227475-10-6
• 化学式: C₁₄H₂₃NO₂S
• 分子量: 269.408
• InChiKey: QVYMUMUWNMPIDG-QXMHVHEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,4-噻唑烷二酮 、 十一醛 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以60%的产率得到(Z)-5-undecylidenethiazolidine-2,4-dione
  参考文献：
  名称：

  Synthesis and evaluation of thiazolidinedione and dioxazaborocane analogues as inhibitors of AI-2 quorum sensing in Vibrio harveyi

  摘要：

  Two focused libraries based on two types of compounds, that is, thiazolidinediones and dioxazaborocanes were designed. Structural resemblances can be found between thiazolidinediones and well-known furanone type quorum sensing (QS) inhibitors such as N-acylaminofuranones, and/or acyl-homoserine lactone signaling molecules, while dioxazaborocanes structurally resemble previously reported oxazaborolidine derivatives which antagonized autoinducer 2 (AI-2) binding to its receptor. Because of this, we hypothesized that these compounds could affect AI-2 QS in Vibrio harveyi. Although all compounds blocked QS, the thiazolidinediones were the most active AI-2 QS inhibitors, with EC50 values in the low micromolar range. Their mechanism of inhibition was elucidated by measuring the effect on bioluminescence in a series of V. harveyi QS mutants and by DNA-binding assays with purified LuxR protein. The active compounds neither affected bioluminescence as such nor the production of AI-2. Instead, our results indicate that the thiazolidinediones blocked AI-2 QS in V. harveyi by decreasing the DNA-binding ability of LuxR. In addition, several dioxazaborocanes were found to block AI-2 QS by targeting LuxPQ. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.11.055

文献信息

• [EN] NOVEL ANTI-BIOFILM AGENTS<br/>[FR] NOUVEAUX AGENTS ANTI-BIOFILMS
  申请人：YISSUM RES DEV CO

  公开号：WO2010058402A1

  公开（公告）日：2010-05-27

  Novel agents exhibiting anti-biofilm formation activity while being non-cytotoxic are provided, as well as methods of using the same, either per se or conjugated to a polymer, for preventing and/or reducing the formation of microbial biofilms and/or for disrupting microbial biofilms. The novel agents described herein include thiazolidine-2,4-diones (TZDs), pyrrolidine -2, 5- diones (PYDs), imidazolidine-2, 4 -diones or oxazolidine-2,4-diones, substituted by an alkylidene having 7-20 carbon atoms in its backbone chain.

  提供了一种表现出抗生物膜形成活性且无细胞毒性的新型药剂，以及使用这些药剂的方法，可以直接使用或与聚合物结合，用于预防和/或减少微生物生物膜的形成和/或破坏微生物生物膜。本文描述的新型药剂包括噻唑烷-2,4-二酮（TZDs）、吡咯烷-2,5-二酮（PYDs）、咪唑烷-2,4-二酮或噁唑烷-2,4-二酮，其通过具有7-20个碳原子的烷基烯链进行取代。
• NOVEL ANTI-BIOFILM AGENTS
  申请人：Srebnik Morris

  公开号：US20110281921A1

  公开（公告）日：2011-11-17

  Novel agents exhibiting anti-biofilm formation activity while being non-cytotoxic are provided, as well as methods of using the same, either per se or conjugated to a polymer, for preventing and/or reducing the formation of microbial biofilms and/or for disrupting microbial biofilms. The novel agents described herein include thiazolidine-2,4-diones (TZDs), pyrrolidine-2,5-diones (PYDs), imidazolidine-2,4-diones or oxazolidine-2,4-diones, substituted by an alkyl having 7-20 carbon atoms in its backbone chain.

  本发明提供了一种表现出抗生物膜形成活性且非细胞毒性的新型药剂，以及使用它们的方法，无论是自身还是与聚合物结合，用于预防和/或减少微生物生物膜的形成和/或破坏微生物生物膜。本发明所描述的新型药剂包括噻唑啉-2,4-二酮（TZDs）、吡咯烷-2,5-二酮（PYDs）、咪唑啉-2,4-二酮或噁唑啉-2,4-二酮，其被一个含有7-20个碳原子的烷基取代。
• Novel anti-biofilm agents
  申请人：Yissum Research Development Company of The Hebrew University of Jerusalem Ltd.

  公开号：EP2365969B1

  公开（公告）日：2017-03-22
• US8865909B2
  申请人：——

  公开号：US8865909B2

  公开（公告）日：2014-10-21
• Synthesis and evaluation of thiazolidinedione and dioxazaborocane analogues as inhibitors of AI-2 quorum sensing in Vibrio harveyi
  作者：Gilles Brackman、Abed Al Aziz Al Quntar、Claes D. Enk、Izet Karalic、Hans J. Nelis、Serge Van Calenbergh、Morris Srebnik、Tom Coenye

  DOI：10.1016/j.bmc.2012.11.055

  日期：2013.2

  Two focused libraries based on two types of compounds, that is, thiazolidinediones and dioxazaborocanes were designed. Structural resemblances can be found between thiazolidinediones and well-known furanone type quorum sensing (QS) inhibitors such as N-acylaminofuranones, and/or acyl-homoserine lactone signaling molecules, while dioxazaborocanes structurally resemble previously reported oxazaborolidine derivatives which antagonized autoinducer 2 (AI-2) binding to its receptor. Because of this, we hypothesized that these compounds could affect AI-2 QS in Vibrio harveyi. Although all compounds blocked QS, the thiazolidinediones were the most active AI-2 QS inhibitors, with EC50 values in the low micromolar range. Their mechanism of inhibition was elucidated by measuring the effect on bioluminescence in a series of V. harveyi QS mutants and by DNA-binding assays with purified LuxR protein. The active compounds neither affected bioluminescence as such nor the production of AI-2. Instead, our results indicate that the thiazolidinediones blocked AI-2 QS in V. harveyi by decreasing the DNA-binding ability of LuxR. In addition, several dioxazaborocanes were found to block AI-2 QS by targeting LuxPQ. (C) 2012 Elsevier Ltd. All rights reserved.